Try Me
by redwolfbane
Summary: My version of Sam and Jess first meeting at Stanford. Set before Supernatural based mostly from Jessica's point of view. Enjoy :)
1. Try Me

If he hadn't been over six foot, Jessica would have thought he was in high school. Dark hair fell in his eyes when he moved his head masking the hazel eyes behind. Jessica thought he looked almost like an out of place child when she first saw him but as he approached her, tagging behind her friend Brady, she realized just how huge he really was.

She pretended that she hadn't been watching him as they neared; trying to engage in the other girls' conversation in an attempt to avoid the inevitable confrontation.

Granted, Jessica thought he was somewhat attractive and that his weary smile seamed genuine, but she had had enough experience with boys to formulate her belief that they all had the same motives when it came to women. She didn't need another one to deal with - she was only four weeks into her first semester at Stanford and had more after her then she could turn down at once.

"Jessica!"

She turned, pretending she hadn't seen them walk up, and smiled in an attempt to not look disappointed that the boys were now going to follow her for the rest of the party.

"Hey Brady." She smiled in an attempt to look pleased to see her friend and his companion.

She barely kept herself from glaring at the short, blonde boy looked her up and down slowly before continuing.

"Well, you look fine as ever, Jessie." He winked at her. She'd only known Brady for a few weeks, but he'd been one of her first _friends_ at Stanford considering the fact that she was a freshman. Brady was a sophomore and had showed her around the nursing program when she had arrived so she felt almost indebted to his friendship... that didn't change the fact that she hated the way he looked at her.

The only response she let herself give him for his lewd behavior was no response at all. She simply tried to nonchalantly pull her skirt further down, and pull her hair in front of her.

"Oh, so, anyways," Brady continued, motioning to the giant of a man behind him. "This is Samuel Winchester, he's one of my buddies so I thought I'd introduce you two."

Jessica smiled wearily. "Nice to meet you, I'm Jessica."

Jessica hadn't dared look at Brady's friend in the face since they had approached and now as she did, she was shocked by his monstrous height and the much more prominent features that defined this, 'Samuel'.

Her new estimate of his height was about 6' 4", standing well over most of the party's occupants. He was built and strong, seeming to dwarf his companion in height and build. His face was long, chiseled and defined around high cheek bones and deep-set, hazel eyes. Dark brown hair framed his face and fell in his eyes as he looked away from her gaze.

She felt extremely awkward as she suddenly realized that he had looked away because she was staring at him.

She took another sip of her drink realizing for the first time since she had been introduced to Samuel that Brady was actually still talking.

"...So, I'm gonna go get Holley. Jessie, will you watch him for me?"

Before she could answer, Brady was already pushing back through the crowd, leaving Samuel with her.

"I'm so sorry he interrupted your conversation, I didn't know he was going to do that..." Samuel spoke up once their mutual friend was out of ear shot.

Jessica noticed a worried smile playing at the corner of his smile and realized as she heard his soft voice that he was actually shy. She wouldn't have pegged him as such with a build of an athlete and had expected him to have mannerisms of such.

She grinned, trying to make him feel less awkward then he obviously already did. She glanced over her shoulder, but her girlfriends had left sometime during Brady's interruption.

Turning back to her new charge, she shrugged. "I didn't really know them anyways. Don't worry about it, Samuel."

Thrusting his hands into the pockets of his oversized Carhart, the boy cleared his throat.

"It's Sam." He then added quickly with a mumble. "If that's okay."

She couldn't help but laugh and he looked at her with obvious worry.

"Sam, you don't have to ask if it's okay for someone to call you by the name you prefer."

He shuffled his feet with a sheepish smile, as his somewhat of a snub nose wrinkled a little.

"Yeah, that sounded a little dumb, huh?" he admitted avoiding her eyes in embarrassment.

Worried that she had made him feel dumb, she shook her head.

"No it's fine! I hate the name Jessie, so, I get it."

"What do you like?" Sam asked in all sincerity.

Jessica thought for a moment. She hadn't had to answer this question for these first four weeks she'd been at Stanford, Brady had always introduced her and when she had introduced herself she'd always said Jessica, but now she actually considered.

"Jess," she admitted, finally feeling good to leave the name her dad had always called her and the childhood Jessie that she detested.

Sam nodded, "I'll remember that."

Silence followed and she felt the awkwardness of first meetings again. She thought that this Sam seemed like a good guy, but the fact that he was friends with Brady proved otherwise.

"How do you know Brady?"

The question was sudden, taking her off guard.

"Oh," she thought, "I, ah, met him in my Biology class."

Sam knit his brow, "He made it sound like you had known him for a lot longer."

Jessica gave a wry chuckle to this prospect. "He would. Did you come to school with him?"

It was Sam's turn to grin. "Ah, no. I met him yesterday, actually. He introduced himself out of the blue and then had me come tonight, I don't know."

She didn't know why, but suddenly she felt her chest lighten and a sigh of relief left her lips. Why she was relieved that he wasn't Brady's friend was beyond her comprehension but she found it so much easier to look him in the eye.

"Well, don't get to know him too well, he's kind of a jerk." she warned in all earnest.

Sam's eyebrows bent up in concern and she could have sworn he looked worried as he eyed her.

"Yeah, I caught that. Is he not your boyfriend?"

Jessica practically choked on her Coke. "No. Not in a thousand years."

Sam's frown deepened as he nodded slowly. "Are you okay, then? Because he seemed like he... was..."

Jessica grinned at this stranger's deep-set, genuine concern for her safety. She wondered what kind of childhood he'd had to immediately think that she was in danger because of one college boy's inappropriate behavior.

"No, Sam, I'm fine he's all talk, I'm used to it."

"Just because you are used to it, doesn't make it right."

Jessica stared at him in pure shock until his eyes morphed from concerned to questioning of her stare.

"Where did you come from, Sam Winchester?"

Obviously not understanding the tone of her reverent question, he replied automatically.

"Lawrence Kansas, Miss."

Her laugh made him question what he had said out of instinct and he eyed her skeptically.

"There are no men like you here."

He shuffled and shook his head, "There's plenty of pre-law students..."

"But even the pre-law students don't _really_ care about the right. Your parents must have raised you good."

She was surprised by a sarcastic chuckle. "Now that's a long story."

Jessica set her solo cup down and eyed the rest of the moronic college party kids. She hadn't wanted to come to the party anyways, she had only come because Brady said he would introduce her to more people in the med program and she had consented.

"Ya know what?" Jessica eyed his casual smile. "I don't even what to be here, so I've got a lot of time tonight for that story."

He shook his head. "You wouldn't believe me even if I told you..."

Standing and walking towards the door, him at her side, she grinned up at him.

"Try me."

But she never saw his saddened smile as he shook his head.


	2. Scared of the Dark

Scared of the Dark

It was the usual cover, except, she asked so many questions that Sam had to make up new stories and explanations to fit the lie. He realized that he was telling her such a close version to the truth that she was actually catching on to the real family drama. He tried to wrap up the story quickly once he realized that he had exposed himself far too much.

"I'm so sorry about your mom." Jessica put a hand on his arm and he flinched instinctively. She noted this behavior as another sure sign of his crazy childhood.

"M'sorry." He mumbled. Jessica shook her head and smiled.

"Its fine, Sam. I'm just glad you have Dean, he seems like the best brother you could have with all your family's misfortune..." Jessica couldn't think of another way to put it.

Sam almost chuckled dryly at her comment considering that the last time he'd seen dean they had fought. In fact, the whole story had been twisted to put dean in, granted, an unfair light. As Sam considered it he nodded slowly, anger at dean melting with Jessica's words as he contemplated the story he had just retold to her.

"Yeah, you're right." Sam mused brushing hair from his eyes as he glance up at the blackened sky full of stars. Jessica shifted beside him on the park bench and joined his search of the heavens.

"I wish I was as good of a sister to my younger brother as dean is for you. We aren't that close."

"I'm sure you're just as good as dean, sometimes he can be a real jerk..."

Jessica laughed a little and looked Sam in the eye.

"Everyone's a jerk sometimes, that isn't unique to dean. My brother would argue that I'm a jerk all the time."

Sam reeled back slightly, giving her a skeptical look.

"You just listened to two hours of me complaining... You're not a jerk at all."

She frowned. "it's different with family, sometimes you do the worst to those you love the most. I've done things I'm not proud of."

Sam visibly drooped, considering her words. "Yeah, me too, I don't always treat him the best, but Dean is the best friend I have."

Jessica's nodded with a sad smile. "Maybe my brother will get that one day."

"He will." Sam assured her. He frowned and shivered as a cold breeze made his hair stand on end. A twig snapped and Sam practically jumped expecting some sort of heinous monster. As he had told Jess about his childhood he'd remembered too many things himself. But it was nothing and he turned back an sighed. Dean was probably on a hunt and he suddenly felt sick to his stomach as he wondered if dean was hurt or fighting or really, what dean was doing at all. Chest tightening, Sam wondered about his dad. He'd seen them both last on bad terms and he now actually took the time to think about them since he'd seen them a mounth ago.

"Sam?"

Sam was taken from thought by her soft voice.

"Huh?"

"You're lost in your world..." She smiled, tucking her hair behind her ear.

Sam looked down at his hands and frowned.

"Sorry..."

"It's fine! No... You just look tired..."

Sam shook his head. "I'm fine..."

Jessica pulled her phone from her pocket and glanced at the screen.

"It's two!" She laughed back at Sam, shoving the phone back in her pocket.

"I didn't even realize..." He chuckled.

Jessica stood and stretched a little with a yawn.

Sam followed her lead standing and straightening his jacket.

"I'm sorry we only really talked about me... "

Jess laughed and shrugged, sending her curly golden hair swaying.

"Well, you have so much more things to say. My child hood's just boring..."

Sam grinned. "I doubt that."

She raised an eyebrow. "Well, I guess will just have to talk again so you can find out..."

Sam nodded sincerely. "I was already planning on it."

Jess raised an eyebrow.

"I mean, only if you want, like we don't need to talk again but..." Blushing and thrusting his hands deeper in his pockets Sam avoided Jessica's eyes.

"I'd like that." She smiled in return in an attempt to make him feel less awkward. Sam nodded as they began walking.

"I'll walk you to your dorm, it's dark..."

Jess laughed.

"I can find my way in the dark. It's just across the street, Sam." She playfully elbowed him in the ribs. "You scared of the dark?"

She was surprised by the most genuine laugh shed heard from him yet.

"You could say so. Let's just say I don't have the best luck with the dark."

She have him another grin and replied.

"Maybe I should walk you to your dorm."

Sam shook his head, "I'll be fine, you're the one I'm worried about, my bad luck kinda rubs off."

Jessica laughed as they stared for her dorm. "I think I can withstand your bad luck rubbing off on me."

Sam returned the smile and caught her stare again. "I hope so."

Opening the dorm building door for her, Sam grinned as she walked past.

Placing one hand on the door, Jessica leaned back out.

"He probably misses you." She smiled, eyes shining as she searched his immediately confused face. " I miss my brother... you should check in on dean, he'd love it if you called him. "

Sam chuckled. "Maybe all do that." He lied, knowing full well that Dean didn't want to hear from him.

Jessica leaned back towards the recesses of the shadows of the doorway.

"Goodnight. The party sucked, but nice to meet you..."

Sam stood awkwardly wondering whether to just leave of try Dean-approved, dramatic, first meeting goodnight kiss. After weighing the situation, he decided Jessica was something different, so he nodded his head and backed away slowly, eyes still locked with hers.

"Good night, Jess. Sleep well. I'll see you later."

"Sleep well, Sam Winchester. Don't get too scared of the dark." she winked, before raising a hand for a short wave.

Sam nodded and returned the wave. "You too, Jess..." the door shut behind her as she retreated indoors after giving him one last smile."...be safe."


	3. Coffee or Something

She kicked herself for not getting his number. She was in nursing and he was pre-law, they had no classes in common and didn't run in the same circles. This saying, unless planed, they had next to no chance of seeing each other on the huge campus. She'd wanted to ask for his number that night after the party but she had been too scared. Jessica convinced herself that he was nothing more than a cool guy she had met once, but she found herself unconsciously looking for him in every crowded walk way. She'd see an exceptionally tall, dark haired man and she'd feel her chest tighten as she held her breath, but when he'd turn around, it wouldn't be Sam. Two days passed and each time she was disappointed, it hurt worse and worse. Walking from biology on the third day, Jessica saw Brady and made her way over to him.

"Hey Jessie!" Brady called, sly smirk on his thin lips. "You, me, movie night in my dorm?"

Jess hesitated, taken back by the question and reconsidering asking hers at all.

"I ah, have a chemistry test tomorrow so I got to study..." Jessica lied glancing around at passing students.

Brady grinned. "We'll make a rain-check then." He started to walk away with a wink and she blurted out.

"Have you talked to Sam?"

Brady turned around to face her with a raise of an eyebrow.

"Sure." He replied.

Jessica nodded, dry mouthed and blushing cheeks as she tried to consider what to say next.

But Brady answered her unspoken question.

"And no, Jessie, he hasn't talked or asked about you."

Turning sharply on his heel, Brady disappeared into the stream of students in the hallway.

Jessica stood staring after him embarrassment lost in complete disappointment.

There was a break before her next class, and as Jessica walked towards the cafeteria, she realized that Sam was just another one of her failed attempts at a good guy. She tried to think of what was wrong with her that Sam hadn't thought she was worth pursuing. Frowning to herself, she tried to reason away tears. And as she suppressed the tears, anger took their place and she repeated to herself that if Sam didn't give her a second look, then he must not be worth it to her in the first place.

Regardless of this decision, she still glanced around for the hazel eyes hidden behind dark locks.

But they weren't there.

Resolve had settled in by the end of her food and she decided to call a girlfriend and get her to buy drinks tonight.

As she walked towards pharmacology, a familiar voice yelled her name.

"Jess!" She stopped suddenly, breath leaving her lungs.

Closer now, the voice called her name again. "Jess?"

She turned slowly to face him, trying to suppress the tears that were threatening to return.

"Sam." She barely forced his name through quivering lips. She put on her best smile and blinked her eyes a few times before raising her eyes to his.

Concern was heavy in his eyes as she smiled at him.

"What's wrong? Are you okay?" He asked. Jessica was shocked at his question, trying to comprehend why he had noticed.

"Yeah I'm fine." She replied, trying to force a laugh.

Sam raised a skeptical eyebrow and nodded slowly.

"You sure?"

Jessica laughed.

"What are you up to, Sam?" She tried to jibe at his purpose here and his lips twitched into a small smile.

"Well, I just wanted to maybe grab lunch or coffee or something..."

Jessica considered, and glanced at the stream of students flowing into her class room.

"I'd love to, but, I have my class and don't you have one?"

Sam nodded his silly grin growing as he broke eye contact with her, "I do but, your pharmacology class is the only one that I knew about and so this was my only change to catch you..."

Jessica couldn't help but grin at his admittance of stalker activity.

"Did Brady tell you about my class?"

Sam's face lost it's grin and he glance down at his shoes. "No. Whenever I asked Brady about you he wouldn't tell me anything... I asked him about your classes... And he said you didn't want me to, uh, know. So I completely understand if you don't want to have lunch... I just thought id see for my self when Jen told me where your class was today..."

Her mouth hung open as she stared at him.

"I never said that to Brady!" Her blood pounded in her veins and she worked her jaw. "He's such a bastard! I asked him about you and he said that you hadn't said anything about me! I never said anything like that! I can't believe him!"

Sam's mouth twitched into a smile as he realized she was legitimately ticked off and he relaxed a little confidence building listening to her angry tirade.

"...Ya know?" she continued, "Someday, I'm just gonna kick him so-"

Sam's laughter cut her off and she froze suddenly.

"What?" she snapped.

He shook his head, "Jess, It's only natural that he wouldn't tell you I like you! He doesn't want to spoil _his_ chances..."

Jessica's face turned from enraged to mischievous in two seconds as Sam realized his mistake.

"Well, glad to know that you have it all figured out. I'd say his chances are running pretty slim though..."

Sam's embarrassment at his blatant reveal of his attraction to Jessica was suddenly drained in total shock.

"That right?" he barely choked out.

Her smile grew and she took a step away toward her class room before adding:

"Oh, and after class... I'll take you up on that coffee or something..."


End file.
